(+/-) (1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol | 65083-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-) (1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol
• 英文别名: (+/-)-8a-methyl-(8ar)-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1c,6c-diol；(+/-)-8a-Methyl-(8ar)-1,2,3,4,6,7,8,8a-octahydro-naphthalin-1c,6c-diol；9β-Methyl-Δ⁵⁽¹⁰⁾-octalindiol-(1β,6β)；(1S,6S,8aS)-8a-methyl-2,3,4,6,7,8-hexahydro-1H-naphthalene-1,6-diol
• CAS: 65083-11-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: GEMVWTFQNXYPRO-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-) (1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol 在 吡啶 、 氢氧化钾 、 氨 、 双氧水 、 lithium 、 L-Selectride 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 5α-hydroxy-4aβ-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene
  参考文献：
  名称：

  The synthesis of Fenical and Sims' structure of cycloeudesmol. Stereospecific total syntheses of 7-(1-hydroxy-1-methylethyl)-4a-methyldecahydrocyclopropa[d]naphthalene diastereoisomers.

  摘要：

  DOI：

  10.1021/jo00202a019
• 作为产物：
  描述：

  9-甲基-delta-5(10)-辛-1,6-二酮 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 以86%的产率得到(+/-) (1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol
  参考文献：
  名称：

  Total synthesis of (±)-pallambins C and D

  摘要：

  以(±)-维兰德-米舍尔酮为原料，通过 38 步线性反应，首次完成了 (±)-pallambins C 和 D 的全合成。关键的转化过程如下：Grob 断裂-分子内醛醇环化和硫脲/钯催化的羰基环化。

  DOI：

  10.1039/c2cc34310j

文献信息

• Resolution of allylic alcohols by cholesterol oxidase isolated from Rhodococcus erythropolis
  作者：Serge Dieth、Denis Tritsch、Jean-François Biellmann

  DOI：10.1016/0040-4039(95)00235-5

  日期：1995.3

  The oxidation of non-steroidal compounds by cholesterol oxidase isolated from Rhodococcus erythropolis is reported for the first time. It was regio-, stereo- and enantio-selective. The enzyme oxidized preferentially the 2-cyclohexenyl-1-alcohols whose configuration is (S) at the reaction center.

  首次报道了从红球红球菌中分离出的胆固醇氧化酶对非甾体化合物的氧化作用。它是区域，立体和对映体选择性的。该酶优选在反应中心氧化构型为（S）的2-环己烯基-1-醇。
• 535. The reduction of 9-methyl-Δ⁵⁽¹⁰⁾-octalin-1,6-dione
  作者：C. B. C. Boyce、J. S. Whitehurst

  DOI：10.1039/jr9600002680

  日期：——
• Nasarow; Gurwitsch, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 371; engl. Ausg. S. 354
  作者：Nasarow、Gurwitsch

  DOI：——

  日期：——
• Totalsynthese von (+)-<i>D</i>-Homoöstron-3-methyläther
  作者：Jürg Gutzwiller、Werner Meier、Andor Fürst

  DOI：10.1002/hlca.19770600717

  日期：1977.11.2

  Total Synthesis of (+)‐D‐Homoestrone 3‐methyl etherA novel total synthesis of (+)‐D‐homoestrone 3‐methyl ether (21) is described starting from (S)‐8a‐methyl‐3,4,8,8a‐tetrahydro‐2H, 7H‐naphthalene‐1,6‐dione (1) as a chiral synthon for the rings C and D. The key step involves alkylation of the derived 3 with m‐methoxyphenacyl bromide (4) as an AB‐building block to give the dioxo‐secosteroid 5. Hydrogenation of 5 affords the trans‐decalone 11. As by‐products the epimeric cis‐decalones 12 and 13 were characterized. Cyclization of 11 leads under kinetic control predominantly to the Δ9(11)‐tetraene 14. Catalytic hydrogenation of 14 and subsequent modification in ring D give the title compound 21. It was found that 14 and also the derived Δ8‐isomer 15a add hydrogen from the α‐face of the molecule to an extent of about 80%. The 8α‐D‐homoestrone derivatives 20a and 23 as well as the 9β‐isomers 19a and 22 were characterized.
• The synthesis of Fenical and Sims' structure of cycloeudesmol. Stereospecific total syntheses of 7-(1-hydroxy-1-methylethyl)-4a-methyldecahydrocyclopropa[d]naphthalene diastereoisomers.
  作者：Masayoshi Ando、Shinsei Sayama、Kahei Takase

  DOI：10.1021/jo00202a019

  日期：1985.1